Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides

J Org Chem. 2006 Aug 18;71(17):6678-81. doi: 10.1021/jo061043m.


A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton-Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and alpha-nitroalkenes or beta-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Cyanides / chemistry
  • Molecular Structure
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry*
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry*
  • Stereoisomerism


  • Amides
  • Cyanides
  • Pyrroles
  • Pyrrolidines
  • pyrrole-2-carboxaldehyde
  • pyrrolidine